4-Hydroxytolbutamide

Base Information

• Chemical Name: 4-Hydroxytolbutamide
• CAS No.: 5719-85-7
• Molecular Formula: C12H18 N2 O4 S
• Molecular Weight: 286.352
• Hs Code.: 29350090
• UNII: 52K8J94779
• DSSTox Substance ID: DTXSID30205824
• Nikkaji Number: J545.263E
• Wikidata: Q27132812
• Metabolomics Workbench ID: 38884
• ChEMBL ID: CHEMBL3942720
• Mol file: 5719-85-7.mol

Synonyms:1-butyl-3-(4-hydroxymethylphenyl)sulfonylurea;hydroxymethyltolbutamide;methylhydroxytolbutamide;N-((butylamino)carbonyl)-4-(hydroxymethyl)benzenesulfonamide

Chemical Property of 4-Hydroxytolbutamide

Chemical Property:

• Appearance/Colour: WHITE TO OFF-WHITE
• Vapor Pressure: 1.02E-09mmHg at 25°C
• Melting Point: 100-102ºC
• Boiling Point: °Cat760mmHg
• PKA: 4.96±0.10(Predicted)
• Flash Point: °C
• PSA: 103.88000
• Density: 1.268 g/cm³
• LogP: 2.82950
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 12 mg/mL
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 286.09872823
• Heavy Atom Count: 19
• Complexity: 370

Purity/Quality:

98%,99%, ^*data from raw suppliers

Hydroxytolbutamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)CO
• Description: 4-hydroxy Tolbutamide is a cytochrome P450 2C8 (CYP2C8) and CYP2C9 metabolite of tolbutamide, a first-generation potassium channel blocker. Tolbutamide 4-hydroxylation is an often used probe reaction in the pharmaceutical industry for the characterization of CYP2C8 and CYP2C9 involvement in the metabolism of clinical drugs.
• Uses: 4-Hydroxytolbutamide has been used as a standard to assay the fungal biotransformation of tolbutamide to 4′-hydroxytolbutamide.

Technology Process of 4-Hydroxytolbutamide

There total 6 articles about 4-Hydroxytolbutamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

methyl 4-butylaminocarbonylaminosulfonylbenzoate (88241-94-5) → 4-hydroxytolbutamide (5719-85-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1.) -78 deg C, 6 h; 2.) 0 deg C, overnight;

DOI:10.1248/cpb.31.2518

Reference yield: 21.0%

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide (64-77-7) → 4-hydroxytolbutamide (5719-85-7)

Guidance literature:

With SoLo-D₂₄₁G unspecific peroxygenase; dihydrogen peroxide; ascorbic acid; In aq. phosphate buffer; acetonitrile; at 30 ℃; for 1h; pH=7; Reagent/catalyst; Catalytic behavior; Enzymatic reaction;

DOI:10.1016/j.tet.2019.02.013

Reference yield:

methyl 4-sulfamoylbenzoate (22808-73-7) → 4-hydroxytolbutamide (5719-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / potassium carbonate / tetrahydrofuran / Heating

2: 80 percent / lithium aluminium hydride / tetrahydrofuran / 1.) -78 deg C, 6 h; 2.) 0 deg C, overnight

With lithium aluminium tetrahydride; potassium carbonate; In tetrahydrofuran;

DOI:10.1248/cpb.31.2518

upstream raw materials:

methyl 4-butylaminocarbonylaminosulfonylbenzoate

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

buprenorphine hydrochloride

methyl 4-sulfamoylbenzoate

Downstream raw materials:

1-butyl-3-(p-formylphenyl)sulphonylurea

Refernces

• 1、 Hemeryck,De Vriendt,Belpaire. "Inhibition of CYP2C9 by selective serotonin reuptake inhibitors: In vitro studies with tolbutamide and (S)-warfarin using human liver microsomes". . p. 947 - 951. Retrieved 1999.
• 2、 Rieutord,Stupans,Shenfield,Gross. "Gliclazide hydroxylation by rat liver microsomes". . p. 1345 - 1354. Retrieved 1995.
• 3、 Zhou, Xiao-Yang,Lu, Xiang-Ran,Li, Ying-Hui,Ma, Ya-Qing,Zhao, Shi-Wen,Wang, Fang,Xu, Ren-Ai,Hu, Guo-Xin,Cai, Jian-Ping. "Identification and Enzymatic Activity Evaluation of a Novel CYP2C9 Allelic Variant Discovered in a Patient". . . Retrieved 2021/03/03.
• 4、 Albertolle, Matthew E.,Kim, Donghak,Nagy, Leslie D.,Yun, Chul-Ho,Pozzi, Ambra,Savas, üzen,Johnson, Eric F.,Guengerich, F. Peter. "Heme-thiolate sulfenylation of human cytochrome P450 4A11 functions as a redox switch for catalytic inhibition". . p. 11230 - 11242. Retrieved 2017/08/08.